Category: imidazoles-derivatives

Crystal structure and NMR study of a bisperoxovanadium complex [NH₄][VO(O₂)₂(ima)] was written by Zhang, Shaowei;Xia, Wen;Yang, Yueyue;Yu, Xianyong;Li, Xiaofang. And the article was included in Journal of Coordination Chemistry in 2017.Application of 26832-08-6 This article mentions the following:

A novel bisperoxovanadium complex, [NH₄][VO(O₂)₂(ima)] (1) (ima = imidazole-4-carboxamide), was synthesized by the reaction of NH₄VO₃ and ima in the presence of H₂O₂, and the structure was characterized by single-crystal x-ray technol. The adjacent [NH₄][VO(O₂)₂(ima)] monomers further constructed a 3D supramol. framework through intra- and intermol. H bonding interactions. The composition of the title complex solution was explored using a combination of multinuclear (¹H, ¹³C and ⁵¹V) magnetic resonance, heteronuclear single quantum coherence (HSQC), and variable temperature NMR in a 0.15 mol L^-1 NaCl/D₂O solution that mimics physiol. conditions. According to NMR exptl. results, a pair of isomers (A and B) are observed in aqueous solution, which are attributed to different types of coordination modes between the metal center and the ligands; Isomer B (the main product) has the same coordination structure as the crystal structure of [NH₄][VO(O₂)₂(ima)]. The ⁵¹V NMR experiment together with single-crystal x-ray diffraction results indicated that Isomer A is the hexacoordinated peroxovanadium species while Isomer B is the heptacoordinated species. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6Application of 26832-08-6).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Application of 26832-08-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Developments in the Reactivity of 2-Methylimidazolium Salts was written by Peixoto, Daniela;Figueiredo, Margarida;Gawande, Manoj B.;Corvo, Marta C.;Vanhoenacker, Gerd;Afonso, Carlos A. M.;Ferreira, Luisa M.;Branco, Paula S.. And the article was included in Journal of Organic Chemistry in 2017.Safety of 1-ethyl-2,3-dimethylimidazolium chloride This article mentions the following:

Unexpected and unusual reactivity of 2-methylimidazolium salts toward aryl-N-sulfonylimines and aryl aldehydes is here reported. Upon reaction with aryl-N-sulfonylimines, the addition product, arylethyl-2-imidazolium-1-tosylamide (3), is formed with moderate to good yields, while upon reaction with aldehydes, the initial addition product (6) observed in NMR and HPLC-MS exptl. anal. is postulated by us as an intermediate to the final conversion to carboxylic acids. Studies in the presence and absence of mol. oxygen allow us to conclude that the imidazolium salts is crucial for the oxidation A detailed mechanistic study was carried out to provide insights regarding this unexpected reactivity. In the experiment, the researchers used many compounds, for example, 1-ethyl-2,3-dimethylimidazolium chloride (cas: 92507-97-6Safety of 1-ethyl-2,3-dimethylimidazolium chloride).

1-ethyl-2,3-dimethylimidazolium chloride (cas: 92507-97-6) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Safety of 1-ethyl-2,3-dimethylimidazolium chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Influence of benzimidazole additives in electrolytic solution on dye-sensitized solar cell performance was written by Kusama, Hitoshi;Arakawa, Hironori. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2004.Related Products of 3012-80-4 This article mentions the following:

The influence of benzimidazole additives on the performance of a bis(tetrabutylammonium)-cis-bis(thiocyanato)bis(2,2′-bipyridine-4-carboxylic acid, 4′-carboxylate)ruthenium(II) dye-sensitized TiO₂ solar cell with an I^–/I₃^– redox electrolyte in acetonitrile was studied by measuring the current-voltage characteristics of >20 different benzimidazole derivatives under AM 1.5 (100 mW/cm²). The benzimidazole additives tested had varying effects on the cell performance. Adding benzimidazole drastically enhanced the open-circuit photovoltage (V_oc) and the fill factor (ff), but reduced the short-circuit photocurrent d. (J_sc) of the solar cell. To determine the reasons for the additive effects on cell performance the phys. and chem. properties of the benzimidazoles were computationally calculated Consequently, the greater the calculated partial charge of the nitrogen atoms in position 3 of the benzimidazole groups, the larger the V_oc, but the smaller the J_sc values. The V_oc values also increased as the mol. size of the benzimidazole derivatives decreased. Also, the greater the absolute difference between the calculated dipole moment of the benzimidazole and acetonitrile, the larger the J_sc value. Probably these properties of the benzimidazoles influenced the extent of interaction between the TiO₂ electrode and electrolyte solvent, which changed the dye-sensitized solar cell performance. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Related Products of 3012-80-4).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Related Products of 3012-80-4

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Angiotensin II is a crucial factor in retinal aneurysm formation was written by Chen, He;Zhao, Xin-yu;Chen, You-xin;Deng, Ting-ting. And the article was included in Experimental Eye Research in 2021.Quality Control of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate This article mentions the following:

Retinal arterial macroaneurysms are characterized by the acquired fusiform or saccular dilatations of the retinal artery. Angiotensin II (Ang II) is a major signal mol. of the renin-angiotensin system, which exerts a range of pathogenic actions that are relevant to retinal vascular abnormalities. We aimed to study the effect of Ang II on retinal vessels and explore its relationship with retinal aneurysmal disease. C57BL/6J male mice were administered Ang II at 1000 ng/kg/min for 28 days, and the mice given saline served as controls. The mice in the treatment group were treated once daily by gastric gavage of candesartan cilexetil (an antagonist of Ang II type 1 (AT1) receptor) at 100 mg/kg/day. The in vivo imaging of murine retinas was performed using fundus photog., optical coherence tomog., fluorescein angiog., and indocyanine green angiog. at 7th, 14th, and 28th days of infusion. At the end of the infusion and treatment, the morphol. changes were evaluated by histopathol. examination and electron microscopy; the levels of related proteins in murine retinas were examined by antibody array and Western blot analyses. We found that Ang II infusion induced aneurysm formation in mice retina, which presented as either solitary aneurysms or retinal arterial beading. The aneurysm formation was often accompanied with vessel leakage. Moreover, Ang II infusion itself may result in increased vascular permeability and ganglion cell and inner plexiform layer thickening. The blockade of AT1 receptors by systemic administration of candesartan cilexetil alleviated the Ang II-induced retinal vasculopathy. The protein level anal. further showed that Ang II upregulated IL-1β, PDGFR-β, and MMP-9 expression, and the expression of IL-1β could be inhibited by AT1 receptor antagonist. Our study provides evidence that Ang II is a crucial factor in retinal aneurysm formation and vessel leakage. It is probably the combined effect of Ang II on vessel inflammatory response, pericyte function, and extracellular matrix remodeling that predisposes the retinal arterial wall to aneurysm formation and blood-retinal barrier breakdown. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Quality Control of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Quality Control of 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Interplay of the intermolecular and intramolecular interactions in stabilizing the thione-based copper(I) complexes and their significance in protecting the biomolecules against metal-mediated oxidative damage was written by Chalana, Ashish;Kumar Rai, Rakesh;Karri, Ramesh;Kumar Jha, Kunal;Kumar, Binayak;Roy, Gouriprasanna. And the article was included in Polyhedron in 2022.Synthetic Route of C8H8N2 This article mentions the following:

The synthesis, characterization, and x-ray structure of mono, tri, and polynuclear copper complexes of benzimidazole-based N-substituted thiones, Bz^MeS^H (10) and Bz^OHS^H (11), and N,N’-disubstituted, Bz^MeS^Me (12) and Bz^OHS^Me (13) are reported here. The x-ray structure analyses of the copper-thione complexes revealed that the coordination behavior and the geometry of the central metal ion in these complexes are significantly dependent on the type of the counteranion used in the reaction. For instance, the reactions of benzimidazole-based thiones with CuCl₂ afforded mononuclear trigonal planar Cu(I) complexes 14, 15, 18, and 19. On contrast, upon reaction with CuSO₄, 10 afforded the trinuclear copper complex 16, in which thione 10 acts as a bridging as well as terminal ligand, giving a six-membered Cu₃S₃ cluster. The chair-form of six-membered Cu₃S₃ ring is further stabilized by six intramol. H-bonding interactions, with overall stabilization energy of 19.28 kcal.mol^-1, between the free NH group of 10 and O atom of the counteranion SO^2-₄. Whereas, when thione 10 was reacted with CuI, a 1-dimensional-polymeric chain-like copper complex 17 was obtained as a thermodynamically stable product, in which both 10 and iodine act as bridging ligand. The 3-dimensional network of complexes revealed that these copper-thione compounds are stabilized by the presence of various types of intermol. and intramol. H-bonding and π – π stacking interactions in the solid state. NBO anal. of the crystal geometries revealed that the strength of these interactions ranging from 0.14 to 5.67 kcal.mol^-1. Also the N-substituted thiones have excellent reactive oxygen species (ROS) scavenging property and, thus, protect biomols. including DNA and protein against Cu(I)-mediated oxidative damage. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Synthetic Route of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Synthetic Route of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Mobility and association of ions in aqueous solutions: the case of imidazolium based ionic liquids was written by Bester-Rogac, Marija;Fedotova, Marina V.;Kruchinin, Sergey E.;Klahn, Marco. And the article was included in Physical Chemistry Chemical Physics in 2016.Application of 35487-17-3 This article mentions the following:

The mobility and the mechanism of ion pairing of 1,1 electrolytes in aqueous solutions were investigated systematically on nine imidazolium based ionic liquids (ILs) from 1-methylimidazolium chloride, [MIM][Cl], to 1-dodecyl-3-methylimidazolium chloride, [1,3-DoMIM][Cl], with two isomers 1,2-dimethylimidazolium chloride, [1,2-MMIM][Cl], and 1,3-dimethylimidazolium chloride, [1,3-MMIM][Cl]. Mol. dynamics (MD) simulations, statistical mechanics calculations in the framework of the integral equation theory using one-dimensional (1D-) and three-dimensional (3D-) reference interaction site model (RISM) approaches as well as conductivity measurements were applied. From experiment and MD simulations it was found that the mobility/diffusion coefficients of cations in the limit of infinite dilution decrease with an increasing length of the cation alkyl chain, but not linearly. The aggregation tendency of cations with long alkyl chains at higher IL concentrations impedes their diffusivity. Binding free energies of imidazolium cations with the chloride anion estimated by RISM calculations, MD simulations and experiments reveal that the association of investigated ILs as model 1,1 electrolytes in water solutions is weak but evidently dependent on the mol. structure (alkyl chain length), which also strongly affects the mobility of cations. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Application of 35487-17-3).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Application of 35487-17-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A quantum-chemical-based guide to analyze/quantify the cytotoxicity of ionic liquids was written by Torrecilla, J. S.;Palomar, J.;Lemus, J.;Rodriguez, F.. And the article was included in Green Chemistry in 2010.Related Products of 79917-89-8 This article mentions the following:

A COSMO-RS descriptor (S_σ-profile) has been used in quant. structure-activity relationship studies (QSARs) based on a neural network for the prediction of the toxicol. effect of ionic liquids (ILs) on a leukemia rat cell line (Log EC₅₀ IPC-81) for a wide variety of compounds including imidazolium, pyridinium, ammonium, phosphonium, pyrrolidinium and quinolinium ILs. S_σ-profile is a two-dimensional quantum-chem. parameter capable of characterizing the electronic structure and mol. size of cations and anions. By using a COSMO-RS descriptor for a training set of 105 compounds (96 ILs and 9 closely related salts) with known biol. activities (exptl. Log EC₅₀ IPC-81 values), a reliable neural network was designed for the systematic anal. of the influence of structural IL elements (cation side chain, head group, anion type and the presence of functional groups) on the cytotoxicity of ∼450 IL compounds The Quant. Structure-Activity Map (QSAM), a new concept developed here, was proposed as a valuable tool for (i) the mol. understanding of IL toxicity, by relating Log EC₅₀ IPC-81 parameters to the electronic structure of compounds given by quantum-chem. calculations; and (ii) the sustainable design of IL products with low toxicity, by linking the chem. structure of counterions to the predictions of IL cytotoxicity in handy contour plots. As a principal contribution, quantum-chem.-based QSAM guides allow the anal./quantification of the non-linear mixture effects of the toxicophores constituting the IL structures. Based on these favorable results, the QSAR model was applied to estimate IL cytotoxicities in order to screen com. available compounds with comparatively low toxicities. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Related Products of 79917-89-8).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Related Products of 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Theoretical estimation of the sublimation enthalpy of azoles was written by Baraboshkin, N. M.;Stratulat, A.-M.;Pivina, T. S.. And the article was included in Russian Chemical Bulletin in 2021.Name: 1-Methyl-4-nitroimidazole This article mentions the following:

The crystal structures of number of azoles were modeled using the quantum chem. and Atom-Atom potential methods. The crystal packing was carried out by the local minimization of the crystal structure in the exptl. space group, for which purpose the energy of the crystalline lattice was described by a set of van der Waals interactions in the form of the Buckingham 6-exp potential and Coulomb electrostatic interactions. The enthalpies of sublimation of the calculated and exptl. crystals are satisfactorily consistent. The prediction for the compounds with earlier unknown enthalpies of sublimation was performed on the basis of the obtained data. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Name: 1-Methyl-4-nitroimidazole).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Name: 1-Methyl-4-nitroimidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Structural Anomalies and Electronic Properties of an Ionic Liquid under Nanoscale Confinement was written by Pham, Tuan Anh;Coulthard, Riley M.;Zobel, Mirijam;Maiti, Amitesh;Buchsbaum, Steven F.;Loeb, Colin;Campbell, Patrick G.;Plata, Desiree L.;Wood, Brandon C.;Fornasiero, Francesco;Meshot, Eric R.. And the article was included in Journal of Physical Chemistry Letters in 2020.Reference of 404001-48-5 This article mentions the following:

Ionic liquids (ILs) promise far greater electrochem. performance compared to aqueous systems, yet key physicochem. properties governing their assembly at interfaces within commonly used graphitic nanopores remain poorly understood. In this work, we combine synchrotron X-ray scattering with first-principles mol. dynamics simulations to unravel key structural characteristics of 1-alkyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([TFSI]^–) ionic liquids confined in carbon slit pores. X-ray scattering reveals selective pore filling due to size exclusion, while filled pores exhibit disruption in the IL intermol. structure, the extent of which increases for narrower slit pores. First-principles simulations corroborate this finding and quant. describe how perturbations in the local IL structure, particularly the hydrogen-bond network, depend strongly on the degree of confinement. Despite significant deviations in structure under confinement, electrochem. stability remains intact, which is important for energy storage based on nanoporous carbon electrodes (e.g., supercapacitors). In the experiment, the researchers used many compounds, for example, 3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5Reference of 404001-48-5).

3-Dodecyl-1-methyl-1H-imidazol-3-ium bis((trifluoromethyl)sulfonyl)amide (cas: 404001-48-5) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).Reference of 404001-48-5

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Efficient synthesis of nucleoside 5′-triphosphates and their β,γ-bridging oxygen-modified analogs from nucleoside 5′-phosphates was written by Sun, Qi;Gong, Shanshan;Sun, Jian;Wang, Chengjun;Liu, Si;Liu, Guodong;Ma, Cha. And the article was included in Tetrahedron Letters in 2014.Formula: C4H7ClN2 This article mentions the following:

Thirteen nucleoside 5′-triphosphates (NTPs) and their β,γ-bridging oxygen-modified analogs (β,γ-CX₂-NTPs, X = H, F, Cl, and Br) have been efficiently synthesized from nucleoside 5′-phosphoropiperidates with 4,5-dicyanoimidazole as the activator. A high-yielding and chromatog.-free protocol for the preparation of both natural and base-modified nucleoside 5′-phosphoropiperidates from the corresponding nucleoside 5′-phosphates was also developed. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3Formula: C4H7ClN2).

1-Methyl-1H-imidazol-3-ium chloride (cas: 35487-17-3) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Formula: C4H7ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem